Reactions of triethylgermyllithium with N,N-dialkylated carboxamides

The reactions of triethylgermyllithium with N,N-dialkylated carboxamides have been investigated. N,N-Dimethylacetamide, N,N-dimethylpivalamide, N,N-diethyltrifluoroacetamide and N,N-diethylbenzamide act on triethylgermyllithium, which is made from bis(triethylgermyl)mercury and lithium in hexane, to release the corresponding acyltriethylgermanes as the principal product. The regioselectivity of the present reactions was found to depend markedly on the reaction conditions and the nature of the acyl fragment of amides. Thus, triethylgermyllithium reacts with N,N-dimethylacetamide as metallating agent to give lithium N,N-dimethylacetamide, if the reaction is carried out in tetrahydrofuran solution. Mechanistic interpretations of these results are discussed.